Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones
A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV–Vis, FT-IR and 1H-NMR spectroscopic techniques....
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2010-08-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.shd.org.rs/JSCS/Vol75/No8/01_4585_4027.pdf |
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| author | NINA TODOROVIĆ GORDANA S. UŠĆUMLIĆ NATAŠA V. VALENTIĆ DUŠAN Ž. MIJIN ALEKSANDAR D. MARINKOVIĆ ADEL S. ALIMMARI |
| author_facet | NINA TODOROVIĆ GORDANA S. UŠĆUMLIĆ NATAŠA V. VALENTIĆ DUŠAN Ž. MIJIN ALEKSANDAR D. MARINKOVIĆ ADEL S. ALIMMARI |
| author_sort | NINA TODOROVIĆ |
| collection | DOAJ |
| description | A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV–Vis, FT-IR and 1H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents. |
| first_indexed | 2024-12-21T21:25:49Z |
| format | Article |
| id | doaj.art-85975fdcecc642feb8f37a58e62e9c40 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 |
| language | English |
| last_indexed | 2024-12-21T21:25:49Z |
| publishDate | 2010-08-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-85975fdcecc642feb8f37a58e62e9c402022-12-21T18:49:46ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51392010-08-0175810191032Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridonesNINA TODOROVIĆGORDANA S. UŠĆUMLIĆNATAŠA V. VALENTIĆDUŠAN Ž. MIJINALEKSANDAR D. MARINKOVIĆADEL S. ALIMMARIA series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV–Vis, FT-IR and 1H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents.http://www.shd.org.rs/JSCS/Vol75/No8/01_4585_4027.pdfarylazo pyridone dyesabsorption spectrasolvent effectsubstituent effecttautomeric equilibration |
| spellingShingle | NINA TODOROVIĆ GORDANA S. UŠĆUMLIĆ NATAŠA V. VALENTIĆ DUŠAN Ž. MIJIN ALEKSANDAR D. MARINKOVIĆ ADEL S. ALIMMARI Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones Journal of the Serbian Chemical Society arylazo pyridone dyes absorption spectra solvent effect substituent effect tautomeric equilibration |
| title | Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones |
| title_full | Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones |
| title_fullStr | Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones |
| title_full_unstemmed | Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones |
| title_short | Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones |
| title_sort | synthesis structure and solvatochromic properties of 3 cyano 4 6 diphenyl 5 3 and 4 substituted phenylazo 2 pyridones |
| topic | arylazo pyridone dyes absorption spectra solvent effect substituent effect tautomeric equilibration |
| url | http://www.shd.org.rs/JSCS/Vol75/No8/01_4585_4027.pdf |
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